Benzyl Bromide → 2-(Benzyloxy)-4-(methoxymethoxy)benzaldehyde

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C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[CH2:20]([O:7][C:8]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

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실험 절차

Oven-dried potassium carbonate (0.272 g, 2 mmol) was added to a solution of 2-hydroxy-4-methoxymethyloxy-benzaldehyde (0.182 g, 1 mmol) in 10 mL of acetonitrile and the mixture was stirred for one hour at RT. Benzylbromide (0.24 mL, 2 mmol) was added and the mixture was refluxed for 10 hours. After disappearance of 2-hydroxy-4-methoxymethy-benzaldehyde (TLC), the solvent was evaporated. The residue was chromatographed over silica using hexanes:EtOAC (5:1). The organic fractions were evaporated to obtain 0.218 g (80%) of yellow oil; TLC Rf0.27 hexanes:EtOAc (5:1), 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H, CHO); 7.81-7.83 (d, 1H, J=8.4 Hz, Ar—H6); 7.46-7.39 (m, 5H, C6H5); 6.7-6.69 (m, 2H, Ar—H3/Ar—H5); 5.21 (s, 2H, O—CH2—O); 5.16 (s, 2H, PhCH2); 3.48 (s, 3H, OCH3); 13C NMR (100 MHz, CDCl3) δ 188.6, 163.9, 162.9, 136.1, 130.5, 128.9, 128.5, 127.6, 120.2, 108.8, 101, 94.4, 70.7; analysis calc'd. for C16H16O4: C, 70.57; H, 5.92; O, 23.5. found: C, 70.35; H, 5.95; O, 23.72.